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Key Documents

18565

Sigma-Aldrich

Bromotripyrrolidinophosphonium hexafluorophosphate

≥95.0% (HPLC), for peptide synthesis

Sinonimo/i:

PyBroP®

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About This Item

Formula empirica (notazione di Hill):
C12H24BrF6N3P2
Numero CAS:
Peso molecolare:
466.18
Beilstein:
6842340
Numero MDL:
Codice UNSPSC:
12352107
ID PubChem:
NACRES:
NA.22

product name

Bromotripyrrolidinophosphonium hexafluorophosphate, ≥95.0% (HPLC)

Livello qualitativo

Saggio

≥95.0% (HPLC)

Forma fisica

solid

Impiego in reazioni chimiche

reaction type: Coupling Reactions

applicazioni

peptide synthesis

Temperatura di conservazione

−20°C

Stringa SMILE

F[P-](F)(F)(F)(F)F.Br[P+](N1CCCC1)(N2CCCC2)N3CCCC3

InChI

1S/C12H24BrN3P.F6P/c13-17(14-7-1-2-8-14,15-9-3-4-10-15)16-11-5-6-12-16;1-7(2,3,4,5)6/h1-12H2;/q+1;-1
CYKRMWNZYOIJCH-UHFFFAOYSA-N

Applicazioni

Catalyst for:
Synthesis of primary amides
Direct dehydrative phosphonium cross coupling
Direct arylation
Pyrrolidide formation by phosphonium salt coupling reagents
It can be used as a coupling reagent:
  • For Suzuki–Miyaura cross-coupling of phenols and arylboronic acids to synthesize biaryls and heterobiaryls.
  • To functionalize pyrimidines (synthesized from 3,4-dihydropyrimidin-2(1H)-ones (DHPMs) via the Kappe dehydrogenation) by using various nucleophiles.
  • To synthesize formamidines by coupling with various primary amines and N,N-diisopropylethylamine.

It can also be used as an activating reagent:
  • For the activation of C-OH bond in tautomerizable heterocycles to form the phosphonium salt which aids the Sonogashira coupling of heterocycles with various alkynes.
  • For the one–pot activation of C-O bond in phenols and further coupling reaction with phosphine oxide or phosphite to form C-P bonds.

Altre note

Reactive peptide coupling reagent suitable for α,α-dialkyl amino acids; Synthesis of depsipeptides

Note legali

PyBroP is a registered trademark of Merck KGaA, Darmstadt, Germany

Pittogrammi

Corrosion

Avvertenze

Danger

Indicazioni di pericolo

Classi di pericolo

Eye Dam. 1 - Skin Corr. 1B

Codice della classe di stoccaggio

8A - Combustible corrosive hazardous materials

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable

Dispositivi di protezione individuale

dust mask type N95 (US), Eyeshields, Gloves


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PyBroP: a convenient activator for the synthesis of formamidines.
Delarue S and Sergheraert C
Tetrahedron Letters, 40(30), 5487-5490 (1999)
T. Kurome et al.
Tetrahedron, 52, 4327-4327 (1996)
Efficient Conversion of Biginelli 3, 4-Dihydropyrimidin-2 (1 H)-one to Pyrimidines via PyBroP-Mediated Coupling.
Kang FA, et al.
The Journal of Organic Chemistry, 70(5), 1957-1960 (2005)
Efficient Pd-Catalyzed Coupling of Tautomerizable Heterocycles with Terminal Alkynes via C-OH Bond Activation Using PyBrOP.
Shi C and Aldrich CC
Organic Letters, 12(10), 2286-2289 (2010)
Nickel-Catalyzed Cross-Coupling of Phenols and Arylboronic Acids Through an In Situ Phenol Activation Mediated by PyBroP.
Chen GJ, et al.
Chemistry?A European Journal, 17(14), 4038-4042 (2011)

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